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iTunes 9 not allowing most smart playlists to automatically sync with iPod

Oh dearie me. This is another major blunder for iTunes 9 - which I cannot see anyone else has noticed yet (but sorry if I couldn't find an existing related post).

Since upgrading to iTunes 9- almost all of my smart playlists (whick worked perfectly before) have disappeared from my iPod. They have also removed themselves from the list in iTunes where I choose which playlists to sync. Yes- I use the 'sync only checked songs & playlists' option (but please don't suggest I manually manage music, as I've been there before).

The problem seems to happen when a smart playlist references 2 or more other (smart or normal) playlists in iTunes. This excludes about 95% of my playlists from syncing in iTunes 9.

Before the upgrade I noticed that iTunes posted an exclamation mark next to any playlist on my iPod that had a rule referencing a playlist in iTunes- but they still sunc perfectly for years. I mean if Apple allowed us to make our own smart playlists only for the iPod- then I would understand- but its the only way I can see to have a playlist for example that plays all favourite but not recently played dance music (regardles of actual genre); nor anything I have moved to a manual playlist called 'not for syncing'.

As a test, I tried an experiment with a new smart playlist which said so long as the song appears in (all) 2 smart playlists- to see when it would become 'syncable'. As would be expected- it was not available to sync. As soon as I deleted the 2nd playlist rule- ie it only had to be in 1 playlist, it became 'syncable'. As soon as I added a 2nd rule again- be it a smart or normal playlist- it became 'unsyncable' again (disappeared from the sync list).

Apple please fix this ASAP. I cannot see this as being desirable behavior in any way, shape or form.

And while you are at it with the new improvements with iTunes 9 playlisting- please add an option to exclude certain 'match' parameters- eg match x and y, but exclude anything that matches z. Besides allowing for much better playlisting, that would (to a degree) also provide a workable workaround to the problem above.

Yours faithfully,

Mike

Macbookpro 2.8, Mac OS X (10.6.2), iTunes 9.0.2 (25)

Posted on Dec 13, 2009 5:34 AM

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6 replies

Dec 13, 2009 5:43 AM in response to glitchrate

I guess I should mention that I am using a 6th gen 160GB classic iPod. On the odd occasion, I have seen it not being recognised as mentioned in other threads here- but after reconnecting it a few times- it has come up.

I am interested to see if other people are seeing the same problem as me here- but would be very surprised if it is iPod model specific- as the actual iTunes list is not allowing to select certain playlists for syncing.

Dec 14, 2009 10:18 PM in response to glitchrate

With iTunes 9 the way songs are handled changed quite a bit. You probably need to adjust the settings on how you're playlists sync, as well as ensure you're songs are tagged correctly. In iTunes 9, Apple introduced a field called "Media Kind". It's on the Option Tab when you Get Info on a song. Ensure you're tracks have the correct Media Kind, as that determines which tab on your iPod settings control the syncing. Example, tracks with Media Kind "Music" can only be synced on Music tab, and tracks with Media Kind "Podcast" can only by synced from "podcast".

After doing this you're probably also going to need to check the options on your smart playlists. Many of mine broke because I had a setting that looked for all the songs in the playlist called "Music", before iTunes 9, and needed to change that to instead look for the "Media Kind" Music.

After that then go into the settings and sync the selected playlists. But realize if you have a playlist that has mixed Media Kinds, you'll need to enable the syncing for each media kind on the respective tab. Hopefully this will help you out some.

Dec 15, 2009 1:18 AM in response to Murphybp2

Cheers for chiming in- but I don't think that will solve this problem. I have no podcasts on my iPod- only mp3s. My problem is I have way too much music in my library- over 300GB. So I have all my iTunes smart playlists- eg genre Dubstep- but then I have an iPod version of each of these eg Dubstep iPod- which says match both criteria- playlist is Dubstep, & playlist is not 'Master not sync'. Every smart playlist on my iPod revolves around this playlist- whose rules are if any of the following 2 criteria match: rating is not between 1&2 stars; playlist is not the normal manual playlist called 'not for iPod sync'- where I drop any mp3s that I don't need on my iPod. This scheme worked perfectly before.

But I am gonna chew on what you said today- maybe there is a clue in there or maybe if I experiment with the 'music' rule. Either way- this is not an improvement- it's about 200 steps back. I still maintain that the problem I am seeing is not intentional coding. Something broke in the codebase & now iTunes 9 has playlist / syncing bugs which need fixing.

Either that, or Apple need to finally release a 500GB iPod- so I can get rid of my iPod specific playlists & sync all my iTunes playlists. Then I would even consider putting podcasts on there as well...;) Heck maybe even some video... crazy idea, I know.

Dec 15, 2009 2:35 AM in response to glitchrate

Take a look at this post. If you have a playlist in the form *Playlist X: Playlist is Y AND Playlist is not Z" then any non-music file in either Y or Z has the potential to "poison" the playlist so that iTunes thinks it should not be listed on the Music sync tab. Sometimes adding the rule *Playlist is Music* to Playlist X may be enough to sort things out, otherwise you may need to redefine or edit Playlist Z to remove the "poison" files.

tt2

Dec 16, 2009 1:09 AM in response to turingtest2

Ahhhh right, gotcha. Thank you both for pointing me in the right direction. Sorry I was a bit slow in understanding this at first. I fixed it by adding media kind is music to the main exclusive playlist.

I retract any comments I made about it being buggy, etc.

Although I do agree with one of the comments in the other post- iTunes should show which playlists are not being allowed to sync with an exclamation or greyed out or something- so we know where the problem is & exactly how many playlists it affects.

For anyone else reading this- see the post mentioned above for more details about this- but you shouldn't have to downgrade to 9.0.1 to fix it. Media kind = music... pfft who'd have thunk it, huh?

iTunes 9 not allowing most smart playlists to automatically sync with iPod

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